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1,2-Benzoldicarboxaldehyd
OPA · OPD · PHTHALALDEHYDE · PHTHALDIALDEHYDE · ORTHO-PHTHALALDEHYDE · 1,2-BENZENEDICARBOXALDEHYDE · O-PHTHALDIALDEHYDE · O-PHTHALDEHYDE
Identifikatoren & physikalische Daten
| CAS No. | 643-79-8 |
|---|---|
| Summenformel | C8H6O2 |
| Durchschnittliche Molmasse | 134,13 g/mol |
| Monoisotopische Masse | 134,03677943 g/mol |
| SMILES | O=Cc1ccccc1C=O |
| InChIKey | ZWLUXSQADUDCSB-UHFFFAOYSA-N |
| PubChem CID | 4807 |
| ChEMBL | CHEMBL160145 |
| ChEBI | CHEBI:70851 |
| EC No. | 211-402-2 |
| DTXSID | DTXSID6032514 |
| Lokaler Name | 1,2-Benzoldicarboxaldehyd |
Chemische & physikalische Eigenschaften
| XLogP | 1,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 34,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 115 |
| Stoffklassen | Other Classes -> Benzaldehydes |
| SpringerMaterials Properties | Crystal structure |
| Pestizide | Environmental transformation -> Pesticide transformation products (metabolite, successor) |
| LogP (Verteilungskoeffizient) | log Kow = 0.510.99 (30 °C) |
| Dichte | Density (at 20 °C): 1.13 g/cm³ |
| Color/Form | Long, pale yellow needles from petroleum ether (MP 56-56.5 °C). Also reported as colorless powder (MP: 54 °C)Yellow needles or crystals from ligroin |
| Löslichkeit | In water, 5 g/100 mL at 20 °CVery soluble in ethyl ether, ethanolSolubility in water, g/100ml at 20 °C: 3.8 (soluble)The solubility of o-phthalaldehyde is 3g/100 mL diisopropyl ether, 5g/100mL deionized water, 20g/100mL chloroform, or 20g/100mL acetone at 20°C. |
| Flammpunkt | 132 °C (270 °F) - closed cup132 °C c.c.>230 °F |
| Siedepunkt | BP: 83 °C at 0.8 mm Hg83-84 °C (0.7501 mmHg) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | 55.8 °C55-58 °C(lit.) |
| Dampfdichte | Relative vapor density (air = 1): 4.6 |
| Dampfdruck | 0.56Pa at 25℃ |
| Brechungsindex | 1.4500 (estimate) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | powder |
| Farbe | yellow |
| pH | 7 (53g/l, H2O, 20℃) |
| Merck | 14,7368 |
| BRN | 878317 |
| Stabilität | Stable. Air sensitive. Incompatible with strong oxidizing agents, strong bases. |
| InChI | 1S/C8H6O2/c9-5-7-3-1-2-4-8(7)6-10/h1-6H |
| InChIKey | ZWLUXSQADUDCSB-UHFFFAOYSA-N |
| SMILES | O=Cc1ccccc1C=O |
| LogP (Verteilungskoeffizient) | 0.99 at 30℃ |
| CAS Datenbank | 643-79-8(CAS DataBase Reference) |
| NIST chemische Informationen | O-phthalaldehyde(643-79-8) |
| EPA chemische Informationen | 1,2-Benzenedicarboxaldehyde (643-79-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH228 (44.3%): Flammable solid [Danger Flammable solids]P210, P240, P241, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P333+P317, P362+P364, P363, P370+P378, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 235 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H301: Toxic if swallowed [Danger Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Chemical: 1,2-BenzenedicarboxaldehydeStatus: Active Update: 19-02-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/27723Phthaldialdehyde: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | Combustible. |
| Gefahrenübersicht | Similar properties and health effects to glutaraldehyde[ACGIH] Severe gastrointestinal tract damage and hematological changes observed in 90-day oral study of ratsDelayed skeletal development observed in rats at doses maternally toxic[NTP] Symptoms reported from occupational exposure to Cidex-OPA (aqueous solution containing 0.56% o-phthalaldehyde) include exacerbation of asthma, anaphylaxis, burns and/or irritation, and dermal hypersensitivity[NTP] Causes burnsInhalation may cause corrosive injuries to upper respiratory tract and lungsMay cause skin sensitizationToxic by ingestion[Alfa Aesar MSDS] Occupational asthma confirmed in an endoscopy unit worker[Malo] See Benzaldehyde. See 2-Methylbenzaldehyde. |
| UN-Einstufung | UN Hazard Class: 8UN Subsidiary Risks: 6.1UN Pack Group: II |
| Chemical Dangers | Reacts with oxidants, amines and strong bases. This generates fire and explosion hazard. |
| Packaging and Labelling | Do not transport with food and feedstuffs. Marine pollutant. |
| Toxic Combustion Products | Special hazards arising from the substance or mixture: Carbon oxides. |
| Hazard Classes and Categories | Flam. Sol. 1 (44.3%)Acute toxicity (Oral) - Category 3 |
| Skin, Eye, and Respiratory Irritations | Recently, the use of ortho-phthalaldehyde (OPA) has been increasing as an alternative to glutaraldehyde(GA)for endoscope disinfection. We detected development of bronchial asthma and contact dermatitis in health care workers (HCW) employed in an endoscopy unit. ... Two of 83 health care workers described mild eye irritation, but no contact dermatitis or bronchitis had newly developed. ... |
| Hazardous Reactivities and Incompatibilities | Incompatible materials: Oxidizing agents, amines, strong bases. |
| Brandbekämpfung | Use carbon dioxide, dry powder, foam, water. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Artificial respiration may be needed. Refer immediately for medical attention.Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse skin with plenty of water or shower for at least 15 minutes. Refer immediately for medical attention.Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention. |
| Sichere Lagerung | Well closed. Separated from oxidants, amines, strong bases and food and feedstuffs. Ventilation along the floor. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing. |
| Brandbekämpfungsverfahren | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary. |
| Lagerbedingungen | Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature 2-8 °C. Light sensitive. Moisture sensitive. Store under inert gas. Keep in a dry place. Storage class (TRGS 510): Non-combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials. |
| Reinigungsverfahren | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal. |
| Entsorgungsverfahren | SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubberContaminated packaging: Dispose of as unused product. |
| Verschüttetes entsorgen | Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Vacuum with specialist equipment or carefully sweep into sealable containers. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Preventive Measures | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Provide appropriate exhaust ventilation at places where dust is formed.Appropriate engineering controls: Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.For more Preventive Measures (Complete) data for o-Phthalaldehyde (6 total), please visit the HSDB record page. |
| Eye Prevention | Wear face shield or eye protection in combination with breathing protection. |
| Fire Prevention | NO open flames. |
| Inhalation Risk | A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C. |
| Ökotoxizitätswerte | LD50Species: Anas platyrhychos (Mallard duck) age 18 weeksoral via capsule 738 mg/kg (95% confidence interval: 390-1763 mg/kg) /99% purity/EC50Species: Pseudokirchneriella subcapitata (Green algae)Conditions: freshwater, staticConcentration: 0.22 mg/L for 96 hrEffect: popuation abundance /formulatilon/Concentration: 0.184 mg/L for 96 hr (95% confidence interval: 0.171-0.2 mg/L)Effect: popuation abundance /98% purity/Species: Daphnia magna (Water flea) age <24 hrConcentration: 0.09 mg/L for 48 hr (95% confidence interval: 0.08-0.12 mg/L)Effect: intoxication, immobilization /99.6% purity/For more Ecotoxicity Values (Complete) data for o-Phthalaldehyde (6 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that o-phthalaldehyde is expected to have very high mobility in soil(SRC). Volatilization of o-phthalaldehyde from moist soil surfaces is not expected(SRC) given an estimated Henry's Law constant of 1.8X10-8 atm-cu m/mole(SRC) based upon its vapor pressure, 5.2X10-3 mm Hg(3), and water solubility, 5.0X10+4 mg/L(3). o-Phthalaldehyde is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Biodegradation data in soil were not available(SRC, 2018).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that o-phthalaldehyde is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.8X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 5.2X10-3 mm Hg(4), and water solubility, 5.0X10+4 mg/L(4). o-Phthalaldehyde is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(5), an estimated BCF of 3(SRC), from a log Kow of 0.51(4) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low. Biodegradation data in water were not available(SRC, 2018).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), o-phthalaldehyde, which has a vapor pressure of 5.2X10-3 mm Hg at 21 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase o-phthalaldehyde is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 17 hours(SRC), calculated from its rate constant of 2.3X10-11 cu cm/molecule-sec at 25 °C(3). o-Phthalaldehyde has an absorption peak at 297 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| Expositionspfade | Serious local effects on contact with eyes and skin. The substance can be absorbed into the body by inhalation of its vapour or dust and by ingestion. |
| Toxizitätsübersicht | IDENTIFICATION AND USE: o-Phthalaldehyde (OPA) is used as disinfectant and reagent in fluorometric determination of primary amines and thiols. HUMAN STUDIES: OPA is a commonly used solution for rapid sterilization of medical equipment. Cases of anaphylaxis following cystoscopy with endoscopes sterilized with this agent have been reported. OPA-induced anaphylaxis following laryngoscopy have also been described. In these patients, OPA-specific IgE was detected in the serum. Contact dermatitis occurred in 4 workers of the endoscopy unit, one of whom also developed asthma. Among 80 female disinfection workers who used only antiseptic solutions containing OPA, the incidence of disinfection-related complaints were 10% skin, 9% eye, and 16% respiratory symptoms. ANIMAL STUDIES: In male mice, injected OPA induced specific IgE and IgG in the sera, suggesting that OPA acts as a hapten. Overall, OPA caused acute inflammation and acted as a haptenic allergen, although it caused only mild liver injury. In mice sensitized to ovalbumin (OVA), OPA enhanced the OVA-induced recruitment of neutrophils to the lung and the production of allergen-specific IgE, suggesting that OPA acts as an immunological adjuvant. The major targets from OPA exposure in rats and mice included the respiratory system (nasal cavity, larynx, trachea, and lung), skin, eye, testis, and epididymis. The most sensitive measure of OPA inhalation toxicity in male and female rats and mice was significantly increased incidences of nasal cavity lesions (lowest-observable-effect concentration = 0.44 ppm). OPA was mutagenic in Salmonella typhimurium strain TA100 in the absence of exogenous metabolic activationno mutagenicity was seen in TA100 with metabolic activation or in TA98 or Escherichia coli WP2 uvrA/pKM101, with or without metabolic activation. |
| Signs and Symptoms | Cough. Shortness of breath. Headache.Redness. Pain. Serious skin burns.Redness. Pain. Severe burns.Burns in mouth and throat. Nausea. Diarrhoea. Vomiting. |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Status of Agents Search page, which tabulates the results and current status of tests such as "Short-Term Toxicity Studies", "Long-term Carcinogenicity Studies", "Developmental Studies", "Genetic Toxicology Studies", etc., performed with this chemical. Testing status for o-phthalaldehyde is available.[Available from, as of February 1, 2019: https://ntpsearch.niehs.nih.gov/?e=True&ContentType=Testing+Status]EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPAICSS Dashboard ApplicationAvailable from, as of February 4, 2019: http://actor.epa.gov/dashboard/] |
| Effluent Concentrations | URBAN/SUBURBAN: Phthalaldehyde (isomer unspecified) was detected in air samples collected in 1973 from Denver, CO at a median of 130 ng/cu m(1). |
| ICSC Environmental Data | The substance is very toxic to aquatic organisms. The substance may cause long-term effects in the aquatic environment. It is strongly advised not to let the chemical enter into the environment. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of o-phthalaldehyde can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that o-phthalaldehyde is expected to have very high mobility in soil(SRC). |
| Human Toxicity Excerpts | /CASE REPORTS/ Iatrogenic injury from medical disinfectants is an uncommon but potentially devastating complication. We report an unusual, but severe, upper aerodigestive complication from the use of ortho-phthalaldehyde solution, a commonly used endoscope disinfectant./CASE REPORTS/ PURPOSE: Ortho-phthalaldehyde (Cidex OPA) is a commonly used solution for rapid sterilization of flexible endoscopic equipment. We report two cases of anaphylaxis following cystoscopy with endoscopes sterilized with this agent. Only a handful of such reactions have been reported in the published literature, the majority of which are in the bladder cancer population undergoing surveillance cystoscopy. PATIENTS AND METHODS: We reviewed the clinical presentation of two cases of anaphylaxis following flexible cystoscopy with instruments sterilized with ortho-phthalaldehyde. We further describe their subsequent evaluation by an allergy and immunology specialist who performed skin testing to confirm a suspected ortho-phthalaldehyde allergy. RESULTS: Both patients were skin test positive to ortho-phthalaldehyde antigen. As a result, sterilization techniques for our flexible endoscopes has been altered. To date, no further anaphylactic reactions have occurred in our bladder cancer patients, including the two cases presented herein following subsequent cystoscopic evaluations. CONCLUSIONS: Ortho-phthalaldehyde-sterilized cystoscopes have been associated with anaphylactic reactions in a small number of patients who have undergone repeated cystoscopy. The manufacturer has already made recommendations to avoid this agent in bladder cancer patients. It may be prudent to extend this practice to other populations undergoing repeat cystoscopy./CASE REPORTS/ Ortho-phthalaldehyde (OPA) has recently been used as a disinfectant for various medical apparatuses. OPA is not generally recognized as a potential allergen. CASE SUMMARY: Subsequent to our recent report describing a patient presenting with OPA-induced anaphylaxis following laryngoscopy, we experienced two more such cases. In all three cases, the basophil histamine release test was useful for identifying the allergen as OPA. OPA-specific IgE was successfully detected in the serum of the patients by ELISA. DISCUSSION: Physicians and co-medical workers need to be aware of potential allergens to which patients may be exposed during routine medical procedures./CASE REPORTS/ Because body fluids and blood have a tendency to adhere to transesophageal echo devices, a high level of sterilization is required when cleaning them. Ortho-phthalaldehyde (OPA) has been widely used in Japan since being approved as a high-level sterilant. The authors report a patient with widespread, severe skin and mucous membrane damage of the lip, tongue, pharynx and esophagus areas that was attributed to inadequate washing after the sterilization of a transesophageal echo device with OPA. This patient experienced sequelae, which did not improve after more than 1 year of continuous treatment. When using medical devices sterilized with OPA, the use of a probe cover, when applicable, is recommended and complete washing prior to use is required.For more Human Toxicity Excerpts (Complete) data for o-Phthalaldehyde (10 total), please visit the HSDB record page. |
| Artificial Pollution Sources | o-Phthalaldehyde's production and use as a disinfectant(1) may result in its release to the environment through various waste streams(SRC). |
| F | 1-8-10 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN2923 8/PG 2 |
| Zollcode | 29122900 |
| RTECS-Nr. | TH6950000 |
| R-Sätze (R) | 36/37/38-43-34-25-50-52/53 |
| Toxizität | LD50 orally in Rabbit: 178 mg/kg LD50 dermal Rat > 2000 mg/kg |
| Gefahrensymbole | Xi,T,N,C |
| hazard_note | Irritant/Air Sensitive |
| Sicherheitshinweise (S) | 26-28-36-45-36/37/39-61-37/39 |
| Gefahrenklasse | 8Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Corr. 1BSkin Sens. 1STOT SE 3 |
| Verpackungsgruppe | Ⅱ |
| Lagerklasse | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Gefahrstoffdaten | 643-79-8(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 480 °C |
Anwendungen & Verwendung
Verwenden
o-Phthalaldehyde can be widely used for precolumn derivatization of amino acids in HPLC separation or Capillary electrophoresis. For flow cytometric measurements of protein thiol groups.
Herstellung & Synthese
synthetische
o-Phthalaldehyde is a high-level chemical disinfectant that is commonly used for disinfection of dental and medical instruments as an alternative to glutaraldehyde, which is a known skin and respiratory sensitizer. A variety of processes for manufacturing o-phthalaldehyde have been reported in the literature. o-Phthalaldehyde is produced by heating pure benzaldehyde and chloroform with potassium hydroxide solution. The resulting solution is further acidified with hydrochloric acid and cooled to yield a colorless powder of o-phthalaldehyde. It is also produced by ozonization of naphthalene in alcohol followed by catalytic hydrogenation. Catalytic oxidation of various chemicals is also used in manufacturing o-phthalaldehyde. o-Phthalaldehyde can be manufactured by oxidation of phthalan by nitrogen monoxide in acetonitrile with N-hydroxyphthalimide as the catalyst to yield 80% to 90%.